Polar solvent compatible polyethersiloxane elastomers

• US 20020037951A1
• Filed: 10/05/2001
• Published: 03/28/2002
• Est. Priority Date: 08/25/1999
• Status: Active Grant

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Firstenberg, Donald E., Kuo, An-Li, Kilgour, John A., Chaiyawat, Atchara
• Granted Patent: US 6,545,085 B2
• Time in Patent Office: Days
• US Class Current: 524/262
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61Q 1/06 Lipsticks
• CPC Class Codes: A61Q 1/10 for eyes, e.g. eyeliner, mascara
• CPC Class Codes: A61Q 15/00 Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/06 Preparations for styling the hair, e.g. by temporary shaping or colouring
• CPC Class Codes: A61Q 5/065 Preparations for temporary colouring the hair, e.g. direct dyes
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 83/12 containing polyether sequences

Abstract

The cross-linked hydrosilylation reaction product of an alkenyl functional silicone compound, a silylhydride functional silicone compound, and one or more allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds exhibits stability, compatibility with polar organic solvents and is useful as a component in personal care compositions.

Claims

1. A silicone elastomer, comprising the cross-linked hydrosilylation reaction product of:

(i) an alkenyl functional silicone compound;

(ii) a silylhydride functional silicone compound; and

(iii) one or more allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds.

2. The composition of claim 1, wherein the composition comprises the cross-linked hydrosilylation reaction product of, based on 100 parts by weight of the combined alkenyl functional silicone compound, silylhydride functional silicone compound and allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds, from 10 parts by weight to 99.9 parts by weight of the combined alkenyl functional silicone compound and silylhydride functional silicone compound and from greater than 0.1 parts by weight to 90 parts by weight of the one or more allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds.

3. The composition of claim 1, wherein the alkenyl functional silicone compound comprises one or more compounds of the formula:

M_aM^vi_bD_cD^vi_dT_eT^vi_fQ_g

wherein;

M is R¹R²R³SiO_1/2;

M^{vi is R4}R⁵R⁶SiO_1/2;

D is R⁷R⁸SiO_2/2;

D^vi is R⁹R¹⁰SiO_2/2;

T is R¹¹SiO_3/2;

T^vi is R¹²SiO_3/2; and

Q is SiO_4/2;

R¹, R², R³, R⁷, R⁸ and R¹¹ are each independently alkyl, aryl or aralkyl;

R⁴, R⁹ and R¹² are each independently monovalent terminally unsaturated hydrocarbon radicals;

R⁵, R⁶ and R¹⁰ are each independently monovalent terminally unsaturated hydrocarbon radicals, alkyl, aryl or aralkyl;

a, b, c, d, e, f and g are each integers wherein;

a, b, e, f, and g are each greater than or equal to 0 and less than or equal to 50, 0≦

c≦

2000, 0≦

d≦

200, and provided that;

(a+b)≦

(2+3e+3f+4g) and ≦

(b+d 30 f)≦

200.

4. The composition of claim 3, wherein R⁴ is a monovalent terminally unsaturated (C₂-C₆)hydrocarbon radical;

R⁵, R⁶, R⁷ and R⁸ are each independently (C₁-C₆)alkyl;

R⁵, R⁶, R⁷ and R⁸ are each independently (C₁-C₆)alkyl;

b is 2;

100≦

c≦

2000; and

a, d, e, f and g are each 0.

5. The composition of claim 3, wherein there are at least two different alkenyl functional silicone compounds.

6. The composition of claim 1, wherein the silylhydride functional silicone compound comprises one or more compounds of the formula:

M_hM^H_iD_jD^H_kT_lT^H_mQ_n

wherein;

M is R¹R²R³SiO_1/2;

M^H is R¹³R¹⁴R¹⁵SiO_1/2;

D is R⁷R⁸SiO_2/2;

D^H is R¹⁶R¹⁷SiO_2/2;

T is R¹¹SiO_3/2;

T^H is R¹⁸SiO_3/2;

Q is SiO_4/2;

R¹, R², R³, R⁷, R⁸ and R¹¹ are each independently alkyl, aryl or aralkyl;

R¹³, R¹⁶ and R¹⁸ are each independently H;

R¹⁴, R¹⁵ and R¹⁷ are each independently H, alkyl, aryl or aralkyl; and

h, i, j, k, l, m, and n are each integers wherein h, i, l, m and n are each greater than or equal to 0 and less than or equal to 50, 0≦

j≦

2000, 0≦

k≦

200, and provided that (h+i)≦

(2+31+3m+4n) and 1.5≦

(i+k+m)≦

200.

7. The composition of claim 6, wherein R¹⁴ and R¹⁵ are each independently (C₁-C₆)alkyl, and more preferably are each methyl;

R¹³ is H;

4≦

i≦

30;

1≦

n≦

15 and h, j, k, l, and m are each 0.

8. The composition of claim 6, wherein R¹⁴, R¹⁵ and R¹⁷ are each independently (C₁-C₁₂)alkyl, R¹³ and R¹⁶ are each H;

h+i=2, 0≦

j≦

100, 2≦

k≦

100 and l, m and n are each 0.

9. The composition of claim 1, wherein the allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compound comprises one or more compounds of the formula:

CH₂—

CH(CH₂)_oO(C_pH_2pO)_q(C_rH_2rO)_sR¹⁹

R₁₉ is hydrogen, alkyl, aryl or acyl;

o, p, q, r and s are each integers wherein;

0≦

o≦

6;

p and r are each independently greater than or equal to 1 and less than or equal to 4;

q and s are each independently greater than or equal to 0 and less than 200 such that 0≦

q+s≦

200.

10. The composition of claim 9, wherein R¹⁹ is (C₁-C₂₀)alkyl.

20. A personal care composition, comprising the silicone elastomer of claim 1.

21. The personal care composition of claim 20, wherein the composition is in the form of water-in-oil emulsion, an oil-in water emulsion or an anhydrous emulsion.

22. The personal care composition of claim 20, further comprising one or more components selected from emollients, pigments, vitamins, sunscreen compounds and sunblock compounds.

23. An antiperspirant composition comprising one or more active anti-perspirant agents and the silicone elastomer of claim 1.

11. A method for making a cross-linked polyether substituted silicone elastomer, comprising forming the hydrosilylation reaction product of (i) an alkenyl functional silicone compound;

(ii) a silylhydride functional silicone compound; and

(iii) one or more allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds.

12. The method of claim 11, wherein the cross-linked polyether substituted silicone elastomer is formed by contacting the alkenyl functional silicone compound, silylhydride functional silicone compound and the one or more allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds under hydrosilylation conditions.

14. The silicone composition of claim 13, wherein the composition is subjected to shear force to break the silicone elastomer into particles.

15. The silicone composition of claim 13, wherein the composition comprises, based on 100 parts by weight of the composition, from 1 part by weight to 99 parts by weight of the liquid medium, from 1 part by weight to 99 parts by weight of the silicone elastomer.

16. The silicone composition of claim 13, wherein the liquid medium comprises an organic liquid and a silicone fluid that is miscible with the organic liquid.

18. The silicone emulsion of claim 17, wherein the first liquid phase comprises a first liquid, the second liquid phase comprises a second liquid and the composition comprises, based on 100 parts by weight of the combined amount of first and second liquids, from 0.1 parts by weight to 99.9 parts by weight of the first liquid, from 0.1 parts by weight to 99.9 parts by weight of the second liquid and, based on 100 parts by weight of the silicone emulsion, from 0.001 parts by weight to 75 parts by weight of the silicone elastomer.

19. The silicone emulsion of claim 18, wherein the first liquid comprises a silicone fluid, an organic liquid or a mixture thereof, and the second liquid comprises water, a substantially polar organic liquid or a mixture thereof.

13. A silicone composition, comprising:

a liquid medium, said liquid medium comprising an organic liquid; and

a silicone elastomer dispersed in the liquid medium, said elastomer comprising the cross-linked hydrosilylation reaction product of (i) an alkenyl functional silicone compound;

(ii) a silylhydride functional silicone compound; and

(iii) one or more allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds.

17. A silicone emulsion, comprising an emulsion of a first liquid phase and a second liquid phase and further comprising a silicone elastomer dispersed in the emulsion, said silicone elastomer comprising the cross-linked hydrosilylation reaction product of (i) an alkenyl functional silicone compound;

(ii) a silylhydride functional silicone compound; and

(iii) one or more allyl started, hydrogen, alkyl, aryl or acyl terminated polyether compounds.